Nematicidal anthranilic acid derivatives from Laccaria species.

Phytochemistry 2019 Apr 22;160:85-91. Epub 2019 Feb 22.

Institute for Organic and Analytical Chemistry, University of Bremen, Leobener Straße 7, 28359, Bremen, Germany. Electronic address:

Three undescribed natural products, the anthranilic acid derivatives laccanthrilic acids A, B, and C, as well as the known (3S)-1,2,3,4-tetrahydro-3-β-carboline-3-carboxylic acid were isolated from fruiting bodies of Laccaria laccata. The structures were established by 1D and 2D NMR spectroscopy, HR-(+)-ESIMS and chemical synthesis. The absolute configuration of laccanthrilic acids A and B was determined by GC-MS after hydrolytic cleavage and derivatisation of the resulting glutamic acid with methanol and Mosher's reagent and subsequent comparison with authentic synthetic samples of known absolute configuration. The absolute configuration of laccanthrilic acid C was determined by comparison of the CD spectra of laccanthrilic acids B and C with each other. Metabolic profiling of related species showed that the compounds are common in the genus Laccaria. Laccanthrilic acid B exhibited moderate nematicidal effects against Caenorhabditis elegans, which might explain to some degree the beneficial role of these fungi for the growth and survival of their host plants.

Download full-text PDF

Source
http://dx.doi.org/10.1016/j.phytochem.2019.01.008DOI Listing
April 2019
3 Reads
2.547 Impact Factor

Publication Analysis

Top Keywords

absolute configuration
12
laccanthrilic acids
12
laccanthrilic acid
8
acid derivatives
8
configuration laccanthrilic
8
anthranilic acid
8
acid
6
laccanthrilic
5
caenorhabditis elegans
4
determined gc-ms
4
effects caenorhabditis
4
hydrolytic cleavage
4
acids determined
4
gc-ms hydrolytic
4
comparison spectra
4
chemical synthesis
4
spectroscopy hr-+-esims
4
spectra laccanthrilic
4
nmr spectroscopy
4
elegans explain
4

Similar Publications